The label originated in St. Louis, Missouri, in 1953 when then owner, and founder, Bob Koester released a recording of the Windy City Six, a traditional jazz group, under the Delmar imprint.

At concerts in Kansas City, he heard Red Allen, Count Basie, Jimmy Rushing, Tommy Douglas, Lionel Hampton, and Jay McShann.

Koester made acquaintance with a fellow jazz club member, Ron Fister, with whom he opened his first record shop, K & F Sales.

During this period in Chicago, Delmark released albums by, Barney Bigard, Donald Byrd, Jimmy Forrest, George Lewis, Bud Powell, and Ira Sullivan.

Throughout the 1960s and 1970s, Delmark recorded the Art Ensemble of Chicago, Sonny Stitt, Junior Wells,[3] Luther Allison, Arthur Crudup, Jimmy Dawkins, Sleepy John Estes, Buddy Guy, J.

B. Hutto,[4][5] Jimmy Johnson, Magic Sam, Robert Nighthawk, Yank Rachell, Otis Rush, Roosevelt Sykes, and Malachi Thompson.

Delmark has also released albums by Fred Anderson, Frank Catalano, Rob Mazurek, Nicole Mitchell, Ken Vandermark, Roy Campbell, Jr., and Ethnic Heritage Ensemble; and blues musicians including Zora Young, Ken Saydak, Byther Smith, Michael Coleman, Little Arthur Duncan, Eddie C. Campbell, Jimmy Burns, and ragtime musicians including Terry Waldo.